一價銠金屬催化氮-甲氧羰基之1,2-二氫吡啶進行不對稱氫芳基化反應

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dc.contributor吳學亮zh_TW
dc.contributorWu, Hsyueh-Liangen_US
dc.contributor.author林羽宣zh_TW
dc.contributor.authorLin, Yu-Hsuanen_US
dc.date.accessioned2022-06-08T02:42:13Z
dc.date.available2021-08-24
dc.date.available2022-06-08T02:42:13Z
dc.date.issued2021
dc.description.abstract本篇論文探討使用一價銠金屬及掌性雙環[2.2.1]雙烯配基L3c及L11a所形成之催化劑，使用環戊基甲基醚為溶劑，甲醇為質子添加劑，反應使用1,2-二氫吡啶14及四芳基硼鈉15為起始物於80 ℃反應24小時進行不對稱加成反應，生成一系列3號位具有芳基取代的掌性1,2,3,4-四氫吡啶產物16及少量四號位加成產物59之混合物，混合產率18–88%，可單獨鑑定主產物16之鏡像超越值為60–96%。另外，利用掌性1,2,3,4-四氫吡啶化合物(R)-16af及(R)-16bf經雙鍵還原及去保護反應成功得到(+)-Preclamol [(+)-4] 前驅物17，兩步總產率為兩步總產率為27%及46%。zh_TW
dc.description.abstractThis thesis describes an enantioselective 1,2-addition of sodium tetraarylborates 15 to 1,2-dihydropyridine 14 in cyclopentyl methyl ether at 80 ℃ with 5.0 equiv of methanol as an additive in the presence of 3.0 mol % of Rh(I)-catalyst in situ generated from the [RhCl(C2H4)2]2 and chiral bicyclo[2.2.1]heptadiene ligand L3c and L11a. The desired 3-aryl-tetrahydropyridines 16 and a small amount of addition product 59 were generated in 18–88% mixed yields and the ee value of chiral compound 16 is determined independently as 60–96%. In addition, the formal synthesis of (+)-Preclamol precursor 17 was achieved by reduction and deprotection of compound (R)-16af and (R)-16bf in 27% and 46% yield for 2 steps.en_US
dc.description.sponsorship化學系zh_TW
dc.identifier60842057S-40032
dc.identifier.urihttps://etds.lib.ntnu.edu.tw/thesis/detail/9a9ef65ef8a43b6b7025a6be7e0343ba/
dc.identifier.urihttp://rportal.lib.ntnu.edu.tw/handle/20.500.12235/117242
dc.language中文
dc.subject鏡像選擇性zh_TW
dc.subject一價銠金屬催化zh_TW
dc.subject氫芳基化反應zh_TW
dc.subject1zh_TW
dc.subject2‐二氫吡啶zh_TW
dc.subject四芳基硼鈉試劑zh_TW
dc.subject不對稱加成反應zh_TW
dc.subject掌性zh_TW
dc.subject掌性雙環[2.2.1]雙烯配基zh_TW
dc.subjectenantioselectiveen_US
dc.subjectRhodium(I)-catalyzeden_US
dc.subjecthydroarylationen_US
dc.subject1en_US
dc.subject2- dihydropyridinesen_US
dc.subjectsodium tetraarylboratesen_US
dc.subjectasymmetric additionen_US
dc.subjectchiralen_US
dc.subjectchiral bicyclo[2.2.1]diene ligandsen_US
dc.title一價銠金屬催化氮-甲氧羰基之1,2-二氫吡啶進行不對稱氫芳基化反應zh_TW
dc.titleRhodium(I)-Catalyzed Asymmetric Hydroarylation of N-Methoxycarbonyl 1,2-Dihydropyridinesen_US
dc.type學術論文

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